diff --git a/allstarr/Controllers/AdminController.cs b/allstarr/Controllers/AdminController.cs
index 2082452..16a2147 100644
--- a/allstarr/Controllers/AdminController.cs
+++ b/allstarr/Controllers/AdminController.cs
@@ -450,7 +450,8 @@ public class AdminController : ControllerBase
         var decodedName = Uri.UnescapeDataString(name);
         _logger.LogInformation("Removing playlist: {Name}", decodedName);
         
-        var currentPlaylists = _spotifyImportSettings.Playlists.ToList();
+        // Read current playlists from .env file (not stale in-memory config)
+        var currentPlaylists = await ReadPlaylistsFromEnvFile();
         var playlist = currentPlaylists.FirstOrDefault(p => p.Name == decodedName);
         
         if (playlist == null)
@@ -767,6 +768,9 @@ public class AdminController : ControllerBase
             
             var playlists = new List<object>();
             
+            // Read current playlists from .env file for accurate linked status
+            var configuredPlaylists = await ReadPlaylistsFromEnvFile();
+            
             if (doc.RootElement.TryGetProperty("Items", out var items))
             {
                 foreach (var item in items.EnumerateArray())
@@ -784,7 +788,7 @@ public class AdminController : ControllerBase
                         childCount = ric.GetInt32();
                     
                     // Check if this playlist is configured in allstarr and get linked Spotify ID
-                    var configuredPlaylist = _spotifyImportSettings.Playlists
+                    var configuredPlaylist = configuredPlaylists
                         .FirstOrDefault(p => p.Name.Equals(name, StringComparison.OrdinalIgnoreCase));
                     var isConfigured = configuredPlaylist != null;
                     var linkedSpotifyId = configuredPlaylist?.Id;
@@ -909,8 +913,11 @@ public class AdminController : ControllerBase
         _logger.LogInformation("Linking Jellyfin playlist {JellyfinId} to Spotify playlist {SpotifyId} with name {Name}", 
             jellyfinPlaylistId, request.SpotifyPlaylistId, request.Name);
         
+        // Read current playlists from .env file (not in-memory config which is stale)
+        var currentPlaylists = await ReadPlaylistsFromEnvFile();
+        
         // Check if already configured
-        var existingPlaylist = _spotifyImportSettings.Playlists
+        var existingPlaylist = currentPlaylists
             .FirstOrDefault(p => p.Name.Equals(request.Name, StringComparison.OrdinalIgnoreCase));
         
         if (existingPlaylist != null)
@@ -919,7 +926,6 @@ public class AdminController : ControllerBase
         }
         
         // Add the playlist to configuration
-        var currentPlaylists = _spotifyImportSettings.Playlists.ToList();
         currentPlaylists.Add(new SpotifyPlaylistConfig
         {
             Name = request.Name,
@@ -959,6 +965,64 @@ public class AdminController : ControllerBase
         return $"MediaBrowser Client=\"Allstarr\", Device=\"Server\", DeviceId=\"allstarr-admin\", Version=\"1.0.0\", Token=\"{_jellyfinSettings.ApiKey}\"";
     }
     
+    /// <summary>
+    /// Read current playlists from .env file (not stale in-memory config)
+    /// </summary>
+    private async Task<List<SpotifyPlaylistConfig>> ReadPlaylistsFromEnvFile()
+    {
+        var playlists = new List<SpotifyPlaylistConfig>();
+        
+        if (!System.IO.File.Exists(_envFilePath))
+        {
+            return playlists;
+        }
+        
+        try
+        {
+            var lines = await System.IO.File.ReadAllLinesAsync(_envFilePath);
+            foreach (var line in lines)
+            {
+                if (line.TrimStart().StartsWith("SPOTIFY_IMPORT_PLAYLISTS="))
+                {
+                    var value = line.Substring(line.IndexOf('=') + 1).Trim();
+                    
+                    if (string.IsNullOrWhiteSpace(value) || value == "[]")
+                    {
+                        return playlists;
+                    }
+                    
+                    // Parse JSON array format: [["Name","Id","first|last"],...]
+                    var playlistArrays = JsonSerializer.Deserialize<string[][]>(value);
+                    if (playlistArrays != null)
+                    {
+                        foreach (var arr in playlistArrays)
+                        {
+                            if (arr.Length >= 2)
+                            {
+                                playlists.Add(new SpotifyPlaylistConfig
+                                {
+                                    Name = arr[0].Trim(),
+                                    Id = arr[1].Trim(),
+                                    LocalTracksPosition = arr.Length >= 3 && 
+                                        arr[2].Trim().Equals("last", StringComparison.OrdinalIgnoreCase)
+                                        ? LocalTracksPosition.Last
+                                        : LocalTracksPosition.First
+                                });
+                            }
+                        }
+                    }
+                    break;
+                }
+            }
+        }
+        catch (Exception ex)
+        {
+            _logger.LogError(ex, "Failed to read playlists from .env file");
+        }
+        
+        return playlists;
+    }
+    
     private static string MaskValue(string? value, int showLast = 0)
     {
         if (string.IsNullOrEmpty(value)) return "(not set)";
diff --git a/allstarr/wwwroot/index.html b/allstarr/wwwroot/index.html
index d1632ba..05f6874 100644
--- a/allstarr/wwwroot/index.html
+++ b/allstarr/wwwroot/index.html
@@ -329,6 +329,40 @@
             color: var(--text-secondary);
         }
         
+        .restart-banner {
+            position: fixed;
+            top: 0;
+            left: 0;
+            right: 0;
+            background: var(--warning);
+            color: var(--bg-primary);
+            padding: 12px 20px;
+            text-align: center;
+            font-weight: 500;
+            z-index: 9998;
+            display: none;
+            box-shadow: 0 2px 8px rgba(0,0,0,0.3);
+        }
+        
+        .restart-banner.active {
+            display: block;
+        }
+        
+        .restart-banner button {
+            margin-left: 16px;
+            background: var(--bg-primary);
+            color: var(--text-primary);
+            border: none;
+            padding: 6px 16px;
+            border-radius: 4px;
+            cursor: pointer;
+            font-weight: 500;
+        }
+        
+        .restart-banner button:hover {
+            background: var(--bg-secondary);
+        }
+        
         .modal {
             display: none;
             position: fixed;
@@ -478,6 +512,13 @@
     </style>
 </head>
 <body>
+    <!-- Restart Required Banner -->
+    <div class="restart-banner" id="restart-banner">
+        ⚠️ Configuration changed. Restart required to apply changes.
+        <button onclick="restartContainer()">Restart Now</button>
+        <button onclick="dismissRestartBanner()" style="background: transparent; border: 1px solid var(--bg-primary);">Dismiss</button>
+    </div>
+    
     <div class="container">
         <header>
             <h1>
@@ -851,6 +892,18 @@
         // Track if we've already initialized the cookie date to prevent infinite loop
         let cookieDateInitialized = false;
         
+        // Track if restart is required
+        let restartRequired = false;
+        
+        function showRestartBanner() {
+            restartRequired = true;
+            document.getElementById('restart-banner').classList.add('active');
+        }
+        
+        function dismissRestartBanner() {
+            document.getElementById('restart-banner').classList.remove('active');
+        }
+        
         // Tab switching
         document.querySelectorAll('.tab').forEach(tab => {
             tab.addEventListener('click', () => {
@@ -1190,8 +1243,10 @@
                 const data = await res.json();
                 
                 if (res.ok) {
-                    showToast('Playlist linked! Restart container to apply.', 'success');
+                    showToast('Playlist linked!', 'success');
+                    showRestartBanner();
                     closeModal('link-playlist-modal');
+                    // Refresh both tabs to show updated status
                     fetchJellyfinPlaylists();
                     fetchPlaylists();
                 } else {
@@ -1213,7 +1268,8 @@
                 const data = await res.json();
                 
                 if (res.ok) {
-                    showToast('Playlist unlinked. Restart container to apply.', 'success');
+                    showToast('Playlist unlinked.', 'success');
+                    showRestartBanner();
                     fetchJellyfinPlaylists();
                     fetchPlaylists();
                 } else {
@@ -1288,6 +1344,7 @@
                     });
                     if (res.ok) {
                         document.getElementById('restart-status').textContent = 'Server is back! Reloading...';
+                        dismissRestartBanner();
                         setTimeout(() => window.location.reload(), 500);
                         return;
                     }
@@ -1334,7 +1391,8 @@
                 const data = await res.json();
                 
                 if (res.ok) {
-                    showToast('Playlist added. Restart container to apply.', 'success');
+                    showToast('Playlist added.', 'success');
+                    showRestartBanner();
                     closeModal('add-playlist-modal');
                 } else {
                     showToast(data.error || 'Failed to add playlist', 'error');
@@ -1355,7 +1413,8 @@
                 const data = await res.json();
                 
                 if (res.ok) {
-                    showToast('Playlist removed. Restart container to apply.', 'success');
+                    showToast('Playlist removed.', 'success');
+                    showRestartBanner();
                     fetchPlaylists();
                 } else {
                     showToast(data.error || 'Failed to remove playlist', 'error');
@@ -1458,7 +1517,8 @@
                 const data = await res.json();
                 
                 if (res.ok) {
-                    showToast('Setting updated. Restart container to apply.', 'success');
+                    showToast('Setting updated.', 'success');
+                    showRestartBanner();
                     closeModal('edit-setting-modal');
                     fetchConfig();
                     fetchStatus();